Crystal structure of a carcinogen:nucleoside adduct.
The product of reaction between the carcinogen, 7-bromomethyl-12-methylbenz[a]anthracene, and 2'-deoxyadenosine, i.e., N6-(12-methylbenz[a]anthracenyl-7-methyl)deoxyadenosine, has been prepared and characterized, and its structure has been determined by X-ray crystallographic techniques. The major structural features are: (a) the adenine and polycyclic aromatic hydrocarbon residues lie nearly perpendicular to one another; (b) the conformation about the glycosidic bond is syn, rather than anti, and an internal hydrogen bond between the deoxyribose 5'-hydroxyl group and N(3) of the adenine residue is present; and (c) the more planar anthracene portion of the hydrocarbon is stacked between adenine residues of other molecules throughout the crystal.
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*; D001551:Benz(a)Anthracenes / Q000138:chemical synthesis* / Q000378:metabolism; D002273:Carcinogens; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism; D003839:Deoxyadenosines; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D014961:X-Ray Diffraction
D001551:Benz(a)Anthracenes; D002273:Carcinogens; D003839:Deoxyadenosines; C002876:7-bromomethyl-12-methylbenzanthracene; D015127:9,10-Dimethyl-1,2-benzanthracene; C030834:N(6)-(12-methylbenzanthracenyl-7-methyl)deoxyadenosine; D004247:DNA